2-Decarboxy-2-aminomethyl-9-deoxy-9-methylene-5,6-didehydro-PGF1 compounds

ABSTRACT

The present invention particularly relates to novel 2-decarboxy-2-aminomethyl-9-deoxy-9-methylene-5,6-didehydro-PGF 1  compounds and methods for their preparation in pharmacological use.

DESCRIPTION CROSS REFERENCE TO RELATED APPLICATIONS

The present application is a divisional application of U.S. Ser. No. 035,144, filed May 1, 1979, now pending.

BACKGROUND OF THE INVENTION

The present invention particularly relates to novel 2-decarboxy-2-aminomethyl-9-deoxy-9-methylene-5,6-didehydro-PGF₁ compounds and methods for their preparation and pharmalogical use.

The essential material constituting the disclosure of the preparation and pharmacological use of the compounds of the present invention is incorporated here by reference from U.S. Ser. No. 035,144 and U.S. Pat. No. 4,060,534. The latter patent describes certain 9-deoxy-9-methylene-PGF-type compounds which are cis isomers of the novel compounds disclosed herein.

PRIOR ART

Known in the art are trans-5,6-didehydro PG₁ compounds and 9-deoxy-9-methylene PGF compounds. Trans-5,6-didehydro prostaglandins are described in U.S. Pat. Nos. 3,759,978, 3,823,180, 3,832,379, and 3,821,291.

SUMMARY OF THE INVENTION

The present invention particularly provides:

a prostaglandin analog of formula VI ##STR1## wherein Y₁ is trans--CH═CH--, --C.tbd.C--, --CH₂ CH₂ --, or cis--CH═CH--;

wherein M₁ is α--R₅ :β--OH or α--OH:β--R₅, wherein R₅ is hydrogen or methyl;

wherein L₁ is α--R₃ :β--R₄, α--R₄ :β--R₃, or a mixture of α--R₃ :β--R₄ and α--R₄ :β--R₃ wherein R₃ and R₄ are hydrogen, methyl, or fluoro, being the same or different, with the proviso that one of R₃ and R₄ is fluoro only when the other is hydrogen or fluoro;

wherein g is 3, 4, or 5; wherein m is one to 5, inclusive; and

wherein L₂ and L₃ are hydrogen or alkyl of one to 4 carbon atoms, inclusive, being the same or different, or a phramcologically acceptable acid addition salt thereof.

DESCRIPTION OF THE PREFERRED EMBODIMENTS

The present invention particularly relates to the following specific embodiment:

2-decarboxy-2-hydroxymethyl-5,6-trans-didehydro-9-deoxy-9-methylene-16,16-dimethyl-PGF₁. 

I claim:
 1. A prostaglandin analog of formula VI ##STR2## wherein Y₁ is trans--CH═CH--, --C.tbd.C--, --CH₂ CH₂ --, or cis--CH═CH--;wherein M₁ is α--R₅ :β--OH or α--OH:β--R₅, wherein R₅ is hydrogen or methyl; wherein L₁ is α--R₃ :β--R₄, α--R₄ :β--R₃, or a mixture of α--R₃ :β--R₄ and α--R₄ :β--R₃ wherein R₃ and R₄ are hydrogen, methyl, or fluoro, being the same or different, with the proviso that one of R₃ and R₄ is fluoro only when the other is hydrogen or fluoro; wherein g is 3, 4, or 5; wherein m is one to 5, inclusive; and wherein L₂ and L₃ are hydrogen or alkyl of one to 4 carbon atoms, inclusive, being the same or different, or a phramcologically acceptable acid addition salt thereof.
 2. 2-Decarboxy-2-aminomethyl-5,6-trans-didehydro-9-deoxy-9-methylene-16,16-dimethyl-PGF₂, a prostaglandin analog according to claim
 1. 